Potassium Carbonate → 1-{3-Difluoromethoxy-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

HRID 628477Notes

Reaction equation

HRID 628477 reaction equation
Br[CH2:2][C:3]1[C:8]([O:9][CH:10]([F:12])[F:11])=[CH:7][CH:6]=[CH:5][C:4]=1[N:13]1[C:17](=[O:18])[N:16]([CH3:19])[N:15]=[N:14]1.[CH3:20][C:21]1[CH:26]=[C:25]([N:27]2[C:31]([CH3:32])=[C:30]([CH3:33])[C:29]([CH3:34])=[N:28]2)[CH:24]=[CH:23][C:22]=1[OH:35].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:11][CH:10]([F:12])[O:9][C:8]1[C:3]([CH2:2][O:35][C:22]2[CH:23]=[CH:24][C:25]([N:27]3[C:31]([CH3:32])=[C:30]([CH3:33])[C:29]([CH3:34])=[N:28]3)=[CH:26][C:21]=2[CH3:20])=[C:4]([N:13]2[C:17](=[O:18])[N:16]([CH3:19])[N:15]=[N:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 898812151-(2-Bromomethyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-oneHCID 118236550Methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenol

Product 1

HCID 1182904131-{3-Difluoromethoxy-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-bromomethyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 1) 0.30 g, methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenol (described in Reference Preparation example 20) 0.26 g, potassium carbonate 0.21 g and acetonitrile 10 ml was stirred with heating under reflux for six hours. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was then concentrated. The resulting residue was subjected to a silica gel column chromatography to give 1-{3-difluoromethoxy-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Present compound 1”) 0.31 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for six hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was then concentrated

Sources & evidence

ORD record
ord-5d90976b377e47b58560b0781f52fd41
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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